GB1564327A - Indazole derivates - Google Patents
Indazole derivates Download PDFInfo
- Publication number
- GB1564327A GB1564327A GB49834/76A GB4983476A GB1564327A GB 1564327 A GB1564327 A GB 1564327A GB 49834/76 A GB49834/76 A GB 49834/76A GB 4983476 A GB4983476 A GB 4983476A GB 1564327 A GB1564327 A GB 1564327A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- group
- hydrogen
- ylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 119
- 239000001257 hydrogen Substances 0.000 claims description 23
- -1 2-oxazolin-2-yl-amino group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002473 indoazoles Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CEIIXWCAJZTSDA-UHFFFAOYSA-N n-(6-methyl-1h-indazol-5-yl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1=CC=2NN=CC=2C=C1NC1=NCCS1 CEIIXWCAJZTSDA-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 1
- JZDIHLZMJYKFOF-UHFFFAOYSA-N 3-isothiocyanato-1h-indazole Chemical compound C1=CC=C2C(N=C=S)=NNC2=C1 JZDIHLZMJYKFOF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010020852 Hypertonia Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- ODJOWHUVBHWDDK-UHFFFAOYSA-N n-(1-methylindazol-4-yl)-4,5-dihydro-1,3-oxazol-2-amine Chemical compound C1=CC=C2N(C)N=CC2=C1NC1=NCCO1 ODJOWHUVBHWDDK-UHFFFAOYSA-N 0.000 description 1
- ITVZPCRKYKYIEM-UHFFFAOYSA-N n-(1-methylindazol-7-yl)-4,5-dihydro-1,3-oxazol-2-amine Chemical compound C=12N(C)N=CC2=CC=CC=1NC1=NCCO1 ITVZPCRKYKYIEM-UHFFFAOYSA-N 0.000 description 1
- IUWFVAFJSDJKGN-UHFFFAOYSA-N n-(4-chloro-1h-indazol-5-yl)-4,5-dihydro-1,3-oxazol-2-amine Chemical compound C1=CC=2NN=CC=2C(Cl)=C1NC1=NCCO1 IUWFVAFJSDJKGN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1571675A CH605934A5 (en) | 1975-12-03 | 1975-12-03 | Myotonolytic oxazolinyl- and thiazolinyl-amino-indazole derivs. |
| CH1664575A CH605858A5 (en) | 1975-12-22 | 1975-12-22 | Myotonolytic oxazolinyl- and thiazolinyl-amino-indazole derivs. |
| CH927976 | 1976-07-20 | ||
| CH931276 | 1976-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1564327A true GB1564327A (en) | 1980-04-10 |
Family
ID=27429211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49834/76A Expired GB1564327A (en) | 1975-12-03 | 1976-11-30 | Indazole derivates |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4086353A (enExample) |
| JP (1) | JPS5268177A (enExample) |
| AU (1) | AU510820B2 (enExample) |
| BE (1) | BE848962A (enExample) |
| CA (1) | CA1082714A (enExample) |
| DE (1) | DE2653005A1 (enExample) |
| DK (1) | DK528976A (enExample) |
| ES (1) | ES453861A1 (enExample) |
| FI (1) | FI763385A7 (enExample) |
| FR (1) | FR2333504A1 (enExample) |
| GB (1) | GB1564327A (enExample) |
| IE (1) | IE44316B1 (enExample) |
| IL (1) | IL51028A (enExample) |
| NL (1) | NL7613317A (enExample) |
| NO (1) | NO764039L (enExample) |
| NZ (1) | NZ182779A (enExample) |
| PH (1) | PH12642A (enExample) |
| PT (1) | PT65918B (enExample) |
| SE (1) | SE424553B (enExample) |
| YU (1) | YU293876A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9980945B2 (en) | 2015-01-13 | 2018-05-29 | Vanderbilt University | Benzoisoxazole-substituted compounds as MGLUR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4436913A (en) * | 1980-09-05 | 1984-03-13 | Siegfried Aktiengesellschaft | 1H- and 2H- indazole derivatives |
| ES2357502T3 (es) * | 2001-09-26 | 2011-04-27 | Pfizer Italia S.R.L. | Derivados de aminoindazol activos como inhibidores de quinasa, procedimiento para su preparación y composiciones farmaceuticas que los contienen. |
| SE0402763D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Nitro indazole derivatives |
| SE0402762D0 (sv) * | 2004-11-11 | 2004-11-11 | Astrazeneca Ab | Indazole sulphonamide derivatives |
| KR101086967B1 (ko) * | 2005-11-15 | 2011-11-29 | 어레이 바이오파마 인크. | 과다증식성 질환의 치료를 위한 ｅｒｂｂ 유형 ｉ 수용체티로신 키나제 억제제로서의 ｎ4-페닐-퀴나졸린-4-아민유도체 및 관련 화합물 |
| JP2009520825A (ja) * | 2005-12-20 | 2009-05-28 | 武田薬品工業株式会社 | グルコキナーゼ活性剤 |
| WO2009025478A1 (en) * | 2007-08-17 | 2009-02-26 | Lg Life Sciences Ltd. | Indole and indazole compounds as an inhibitor of cellular necrosis |
| JP5188583B2 (ja) * | 2008-01-04 | 2013-04-24 | エルジー・ライフ・サイエンシーズ・リミテッド | 細胞、組織及び臓器保存効果を有するインドール及びインダゾール誘導体 |
| KR101404151B1 (ko) * | 2011-11-25 | 2014-06-05 | 가톨릭대학교 산학협력단 | 안과 질환의 예방 및 치료용 약학 조성물 |
| US10221172B2 (en) | 2015-01-13 | 2019-03-05 | Vanderbilt University | Benzothiazole and benzisothiazole-substituted compounds as mGluR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| WO2016123629A1 (en) | 2015-01-30 | 2016-08-04 | Vanderbilt University | Indazole and azaindazole substituted compounds as mglur4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3759903A (en) * | 1971-07-28 | 1973-09-18 | Squibb & Sons Inc | Thiazolinyl and thiazinyl derivatives of indazoles |
-
1976
- 1976-11-22 DE DE19762653005 patent/DE2653005A1/de not_active Withdrawn
- 1976-11-24 FI FI763385A patent/FI763385A7/fi not_active Application Discontinuation
- 1976-11-24 DK DK528976A patent/DK528976A/da not_active Application Discontinuation
- 1976-11-25 SE SE7613195A patent/SE424553B/xx unknown
- 1976-11-25 NO NO764039A patent/NO764039L/no unknown
- 1976-11-26 US US05/745,303 patent/US4086353A/en not_active Expired - Lifetime
- 1976-11-30 NL NL7613317A patent/NL7613317A/xx not_active Application Discontinuation
- 1976-11-30 GB GB49834/76A patent/GB1564327A/en not_active Expired
- 1976-12-01 NZ NZ182779A patent/NZ182779A/xx unknown
- 1976-12-01 IL IL51028A patent/IL51028A/xx unknown
- 1976-12-01 PH PH19181A patent/PH12642A/en unknown
- 1976-12-01 JP JP51143543A patent/JPS5268177A/ja active Pending
- 1976-12-01 IE IE2637/76A patent/IE44316B1/en unknown
- 1976-12-01 ES ES453861A patent/ES453861A1/es not_active Expired
- 1976-12-01 BE BE172887A patent/BE848962A/xx unknown
- 1976-12-02 YU YU02938/76A patent/YU293876A/xx unknown
- 1976-12-02 CA CA267,015A patent/CA1082714A/en not_active Expired
- 1976-12-02 PT PT65918A patent/PT65918B/pt unknown
- 1976-12-02 FR FR7636296A patent/FR2333504A1/fr active Granted
- 1976-12-03 AU AU20252/76A patent/AU510820B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9980945B2 (en) | 2015-01-13 | 2018-05-29 | Vanderbilt University | Benzoisoxazole-substituted compounds as MGLUR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
Also Published As
| Publication number | Publication date |
|---|---|
| DK528976A (da) | 1977-06-04 |
| IL51028A0 (en) | 1977-02-28 |
| US4086353A (en) | 1978-04-25 |
| JPS5268177A (en) | 1977-06-06 |
| FI763385A7 (enExample) | 1977-06-04 |
| NO764039L (enExample) | 1977-06-06 |
| NZ182779A (en) | 1979-08-31 |
| BE848962A (fr) | 1977-06-01 |
| FR2333504A1 (fr) | 1977-07-01 |
| FR2333504B1 (enExample) | 1980-08-29 |
| IE44316L (en) | 1977-06-03 |
| PT65918B (fr) | 1978-07-05 |
| DE2653005A1 (de) | 1977-06-08 |
| PT65918A (fr) | 1977-01-01 |
| IL51028A (en) | 1980-06-30 |
| NL7613317A (nl) | 1977-06-07 |
| SE424553B (sv) | 1982-07-26 |
| CA1082714A (en) | 1980-07-29 |
| AU510820B2 (en) | 1980-07-17 |
| AU2025276A (en) | 1978-06-08 |
| IE44316B1 (en) | 1981-10-21 |
| YU293876A (en) | 1982-05-31 |
| ES453861A1 (es) | 1978-03-01 |
| PH12642A (en) | 1979-07-11 |
| SE7613195L (sv) | 1977-06-04 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |